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Exercise 7 8/07/2020

Phase separation and purification

1. Solubility tests of benzil and benzoic acid

Reagents: 0.1 g of benzil

water, 2 M NaOH, 2 M HCl, diethyl ether, ethanol, hexane

Table 1. Observations of benzil and benzoic acid solubility in different solvents.

Solvent Solubility of benzil Solubility of benzoic acid

water Not dissolved Almost not dissolved
NaOH Not dissolved Completely dissolved
HCl Almost not dissolved Almost not dissolved
diethyl ether Completely dissolved Completely dissolved
ethanol Slightly dissolved Mostly dissolved, a little bit of precipitate
observed
hexane Not dissolved Almost not dissolved

The aim of this experiment was to find the solvent that will completely dissolve one of the organic
molecules (benzil or benzoic acid) but not another.

We observed that NaOH is the solvent, in which benzil is not soluble, and benzoic acid is completely
dissolved (Table 1), which provide us with enough evidence to use NaOH solution in liquid-liquid
separation. This inference is supported by the knowledge that base NaOH reacts with benzoic acid to
form the benzoate anion, which is soluble in water.

2. The separation of benzil and benzoic acid

Reagents: 2.0 g of the mixture (50% benzoic acid and 50% benzil)

40 mL of ether

10 mL of 2 M NaOH

5 mL of water
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Ether layer

Aqueous layer (with benzoic acid)

Figure 1. Separating funnel with ether and aqueous layer.

The separating funnel was used to separate the ether and aqueous layers (Figure 1). It was followed
by the extraction procedure using sodium hydroxide. Benzil is separated and ready for the recovery
process.

3. Recovery and purification of benzoic acid

Reagents: aqueous layer with benzoic acid

2 M HCl

After the recovery and purification of benzoic acid, the weight of the crystals was 0.19 g. The crystals
look like small needles of white colour with a minimal touch of a ‘yellow tinge’; therefore, they are
not entirely pure due to some possible contamination.

4. Recovery and purification of benzil

Reagents: ether layer with benzil

anhydrous sodium sulphate

After the recovery and purification of benzil, the weight of the crystals was 0.23 g. The crystals look
like small needles of yellow colour with a very small touch of a ‘white tinge’; therefore, they are not
completely pure due to some possible contamination.
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Logbook questions
1. What errors could be made using a separating funnel? How can you avoid them?

The major error using a separating funnel could be close the tap too late allowing for some amount
of the ether layer to run off in the flask. One of the possible solutions to avoid this problem could be
closing the tap before we reach the separating line between two layers. It is better to leave a small
amount of aqueous layer in the separating funnel than to allow the ether layer to move into the
flask.

Some other potential error sources using a separating funnel include:

- not rinsing the funnel properly before the experiment, which can lead to some
contamination,
- not using the correct size of the stopper,
- not opening the tap to release the pressure from the funnel.

To avoid these problems we need to follow the manual precisely and check for all aforementioned
potential mistakes.

2. What did the recrystallised benzoic acid and benzil crystals look like? Do you think they were
‘pure’? Why? How could you check?

The recrystallised benzoic acid and benzil crystals look like needles. These crystals were not 100%
‘pure’ with tinges as probably some contamination has occurred. To test if the substance is pure, it is
possible to use melting point check as impurities will reduce or increase the melting range. The other
option to examine for the purity is analytical methods such as titration, chromatography or
calorimetry.

3. If you started with 2.0 g of benzoic acid (in a 1:1 composition), and benzil, how much of the
purified compounds did you recover as a percentage (i.e. what was the yield of this process)?

We can use the following formula to calculate the yield:

Actual yield
Percentage yield = ∗ 100%
Theoretical yield
2.0 g of the mixture consists of 50% benzoic acid and 50% benzil. Therefore, the theoretical yield for
the benzil and benzoic acid equals 2.0 g/2 = 1.0 g.
For the benzil the percentage yield = (1.0/0.19 g)*100% = 19%
For the benzoic acid the percentage yield = (1.0/0.23 g)*100% = 23%.
These low percentages suggest that we lost quite a significant amount of substances in the
experiment.